1. Field of the Invention
The present invention relates generally to triacylglycerol oligomer products and methods of making, using and producing same.
2. Description of the Related Art
Triacylglycerols (TAGS) are lipids of plant or animal origin. They include such common substances as safflower oil, canola oil, peanut oil, corn oil, cottonseed oil, sunflower seed oil, linseed oil, soybean oil, tung oil, etc. Those TAGS that are liquids at room temperature are generally known as oils; those that are solids are usually known as fats. TAGS are simply the fatty acid esters of the triol glycerol. The general structure of TAGS is: 
The fatty acids, R1, R2, R3, that are obtained by hydrolysis of naturally occurring fats and oils are long, straight-chain carboxylic acids with about 12 to 20 carbon atoms. Most fatty acids contain even number of carbon atoms. Some of these common fatty acids are saturated, while others have one or more elements of unsaturation; generally carbon—carbon double bonds.
TAGS naturally occur in some plants and can be obtained in relative pure forms by various processing methods. Substances such as free fatty acids and phospholipids are removed during processing. TAGS resulting from a single plant source after processing is a mixture made up of TAGS with differing percentages of saturated and unsaturated fatty acids. Table 1 lists the approximate composition of the fatty acids obtained from hydrolysis of some TAGS. Table 2 lists the supply of major TAGS produced in the United States.
TABLE 1Fatty Acid Composition Obtained by Hydrolyhsis of Common Triacylglycerols*TAGMYRISTICPALMITICSTEARICOLEICLINOLEICELEOSTEARICLINOLENICSOYBEAN1–2 6–102–420–3050–58 5–10COTTON1–218–251–217–3845–55SEEDCORN1–2 7–113–425–3550–60LINSEED4–72–414–3014–2545–60SUNFLOWER6–71–221–2266–67TUNG80
TABLE 2Major TAGS produced in the United StatesPRODUCTIONTRIACYLGLYCEROL(POUNDS)SOYBEAN20,220,000,000COTTONSEED1,210,000,000SUNFLOWERSEED1,196,772,000CORN1,283,200,000
TAGS containing multiple double bonds within their carboxylic acid moieties will undergo thermal polymerization to form oligomers which are low molecular weight polymers. Triacylglycerol Oligomers(TAGOS) were first described by Schieber (1928).
Several investigators, Schieber (1928, 1929), Kappelmier (1933, 1938), Kurz (1936), Bradley (1940), Phalnikar and Bhide (1944), Bradley (1947), Barker, Crawford, and Hilditch (1951), Wisenblatt, Wells, and Common (1953), Wells and Common (1953), Pascual and Detera (1966), Boelhouwer, Knegiel, and Tels (1967), Saha and Bandyopadhyay (1974), Sarma (1984) have suggested mechanisms for thermal polymerization of vegetable oils. Scheiber (1928, 1929) and Kappelmeier (1933, 1938) proposed a Diels-Alder diene synthesis as a basis for explaining the polymerization of vegetable oils which is often referred to in the literature. Most investigators agree with the formation of hydroxy unsaturated dimeric acids during thermal polymerization which are connected by means of a cyclic compound.